Synthesis, structures, and solution dynamics of palladium complexes of quinoline-functionalized N-heterocyclic carbenes

Inorganic Chemistry
Hong Mei PengXingwei Li

Abstract

A new type of quinoline-functionalized palladium N-heterocyclic carbene (NHC) complexes has been synthesized via silver transmetallation. The quinoline moiety was either directly attached to the imidazole ring or linked to it by a methylene group. NHCs with a methylene linker tend to form trans biscarbene complexes in the reaction of Pd(COD)Cl2, while NHCs without any linker form chelating NHC-quinoline (NHC-N) complexes. These two types of carbenes also react with [Pd(allyl)Cl]2 to give monodentate NHC palladium eta(3)-allyl chlorides [Pd(NHC)(allyl)Cl]. Fluxionality in the NMR time scale was observed for most complexes, and the origin of their dynamic behaviors was discussed for each type of structure. For [Pd(NHC)(allyl)Cl] with a relatively small wing tip group of the NHC, the fluxionality (selective line-broadening of (1)H NMR signals) is caused by selective eta(3)-eta(1)-eta(3) allyl isomerization. For NHC with a bulkier (t)Bu group, a different line-broadening pattern was observed and was ascribed to partially hindered Pd-C(carbene) bond rotation. For cationic chelating complexes [Pd(NHC-N)(allyl)]BF4, the dynamic exchange process likely originates from a dissociative boat-to-boat inversion of 7-membered palladacycles. A...Continue Reading

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Citations

May 5, 2010·Dalton Transactions : an International Journal of Inorganic Chemistry·Fuwei LiT S Andy Hor
Feb 13, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Abbas Raja NaziruddinWen-Shu Hwang
Feb 7, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Arne FicksLee J Higham
Apr 14, 2009·Chemical Reviews·Joseph C Y LinIvan J B Lin
Apr 5, 2018·Organic Letters·Hiroyuki KitanoKenichiro Itami
Feb 6, 2017·Chemical Reviews·Eduardo Peris

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